Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies

Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies

Thirty-two (32) bis-indolylmethane-hydrazone hybrids 1–32 were synthesized and characterized by 1HNMR, 13CNNMR and HREI-MS. All compounds were evaluated in vitro for β-glucuronidase inhibitory potential. All analogs showed varying degree of β-glucuronidase inhibitory potential ranging from 0.10 ± 0....

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Published in:European Journal of Medicinal Chemistry
Main Author: Taha M.; Ullah H.; Al Muqarrabun L.M.R.; Khan M.N.; Rahim F.; Ahmat N.; Ali M.; Perveen S.
Format: Article
Language:English
Published: Elsevier Masson s.r.l. 2018
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85033591574&doi=10.1016%2fj.ejmech.2017.10.071&partnerID=40&md5=25123fa8f7fff0f74d5ed0f20b7ab3da
id 2-s2.0-85033591574
spelling 2-s2.0-85033591574
Taha M.; Ullah H.; Al Muqarrabun L.M.R.; Khan M.N.; Rahim F.; Ahmat N.; Ali M.; Perveen S.
Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
2018
European Journal of Medicinal Chemistry
143

10.1016/j.ejmech.2017.10.071
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85033591574&doi=10.1016%2fj.ejmech.2017.10.071&partnerID=40&md5=25123fa8f7fff0f74d5ed0f20b7ab3da
Thirty-two (32) bis-indolylmethane-hydrazone hybrids 1–32 were synthesized and characterized by 1HNMR, 13CNNMR and HREI-MS. All compounds were evaluated in vitro for β-glucuronidase inhibitory potential. All analogs showed varying degree of β-glucuronidase inhibitory potential ranging from 0.10 ± 0.01 to 48.50 ± 1.10 μM when compared with the standard drug D-saccharic acid-1,4-lactone (IC50 value 48.30 ± 1.20 μM). Derivatives 1–32 showed the highest β-glucuronidase inhibitory potentials which is many folds better than the standard drug D-saccharic acid-1,4-lactone. Further molecular docking study validated the experimental results. It was proposed that bis-indolylmethane may interact with some amino acid residues located within the active site of β-glucuronidase enzyme. This study has culminated in the identification of a new class of potent β-glucuronidase inhibitors. © 2017 Elsevier Masson SAS
Elsevier Masson s.r.l.
2235234
English
Article
author Taha M.; Ullah H.; Al Muqarrabun L.M.R.; Khan M.N.; Rahim F.; Ahmat N.; Ali M.; Perveen S.
spellingShingle Taha M.; Ullah H.; Al Muqarrabun L.M.R.; Khan M.N.; Rahim F.; Ahmat N.; Ali M.; Perveen S.
Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
author_facet Taha M.; Ullah H.; Al Muqarrabun L.M.R.; Khan M.N.; Rahim F.; Ahmat N.; Ali M.; Perveen S.
author_sort Taha M.; Ullah H.; Al Muqarrabun L.M.R.; Khan M.N.; Rahim F.; Ahmat N.; Ali M.; Perveen S.
title Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
title_short Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
title_full Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
title_fullStr Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
title_full_unstemmed Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
title_sort Synthesis of bis-indolylmethanes as new potential inhibitors of β-glucuronidase and their molecular docking studies
publishDate 2018
container_title European Journal of Medicinal Chemistry
container_volume 143
container_issue
doi_str_mv 10.1016/j.ejmech.2017.10.071
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85033591574&doi=10.1016%2fj.ejmech.2017.10.071&partnerID=40&md5=25123fa8f7fff0f74d5ed0f20b7ab3da
description Thirty-two (32) bis-indolylmethane-hydrazone hybrids 1–32 were synthesized and characterized by 1HNMR, 13CNNMR and HREI-MS. All compounds were evaluated in vitro for β-glucuronidase inhibitory potential. All analogs showed varying degree of β-glucuronidase inhibitory potential ranging from 0.10 ± 0.01 to 48.50 ± 1.10 μM when compared with the standard drug D-saccharic acid-1,4-lactone (IC50 value 48.30 ± 1.20 μM). Derivatives 1–32 showed the highest β-glucuronidase inhibitory potentials which is many folds better than the standard drug D-saccharic acid-1,4-lactone. Further molecular docking study validated the experimental results. It was proposed that bis-indolylmethane may interact with some amino acid residues located within the active site of β-glucuronidase enzyme. This study has culminated in the identification of a new class of potent β-glucuronidase inhibitors. © 2017 Elsevier Masson SAS
publisher Elsevier Masson s.r.l.
issn 2235234
language English
format Article
accesstype
record_format scopus
collection Scopus
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